Ask Polly: How Do I Know If I Should Break Off My Engagement?

Hi Polly,

My fiance and I have been together on and off since we were 18; we are now 26. He was my first boyfriend, first kiss and he is the only person I have had sex with. After dating 20 months I asked for a break to date other people because I thought we were too young, at 20, to be as serious as we were. The beginning of our relationship felt magical. The innocence of first love, having never felt these types of feelings before. I believed in true love and the “one” and knew we’d make it back to each other.

Six months later we did reconnect and began dating again. It lasted only a year. I felt with certainty now that he was the “one” but he now acted ambivalent. His parents had announced their divorce right after I’d ended things with him. He decided to drink away his feelings and now placed his friends above me.

I was still shocked and devastated when he dumped me. He said he still loved me and needed time to figure himself out. I pleaded with him to let us work it out together, I tried to help him see that how he was dealing with his feelings (drinking) wasn’t constructive and urged him to surround himself with better people. In a sense I tried to “save him” because I couldn’t accept that it was over. I struggled with the notion that someone could love you and leave you.

For the next year and a half I allowed him to come in and out of my life. He did many things to hurt me, including lying to me, leading me on, talking badly about me to his friends — and cheating on me. I look back at this now and feel that I did not show myself any self-respect because I was so hung up on the notion of “the one” and idealized our relationship. I also struggled with severe depression and an eating disorder during this period.

Eventually I cut all communication and did not speak to him for nine months. In this time I gradually became better. I made new friends, excelled in school, followed goals and grew as a person. I felt strong enough that I could see him as a friend and rejoin our group of mutual friends that I had missed. Many people would think I was stupid for taking him back after all of this. However, he truly was different and also closer to the person I had fallen in love with. He was honest with me about everything that had happened even when it hurt to hear the truth. He made the relationship a priority again. We moved in together and have lived with one another for two years. We have an easy chemistry and get along very well.

I pushed for the engagement and was initially excited about it, happy to start our future together and be on solid ground. However, a few months after becoming engaged, I started to feel depressed again and eventually entered into an affair with a good friend of mine from university who I have always had some hidden feelings for (it lasted for only three weeks). My fiance was mad when he found out but has decided to work it out with me. He says it made him realize how much he does love me. While he should be furious or fighting with me, he’s been extremely compassionate and stepped up his game, making dinners and sending me cute notes. Truth be told, based on our history, I expected him to leave me. Him not leaving has been reassuring.

I know that you can’t compare a long-term live in relationship to the high of an affair, but it has made me realize that maybe something is missing in my current relationship. The passion is gone and the sex is okay but not great. I fantasize still about sleeping with this other guy just to see what sex is like with someone else. I worry that I still don’t know what truly makes me happy. I also worry that my depression paints things negatively and I’m taking it out on my relationship — because of this I can’t make sense of my own feelings. I don’t like the way he never speaks with certainty. I wish he took more interest in my career or we had more shared passions. I worry that our relationship is based on getting along and having fun and we don’t go deep enough. Alternatively, am I taking for granted having a solid partner who takes care of me and loves me? Is it just depression speaking?

I am in therapy to work this out but it nags at me everyday. The more I spin it around in my head the more I feel bad. I feel bad for treating someone the way I have and for not being sure about someone who is sure about me. I can’t take time off from a relationship that has had so many breaks. Either we get married or we break up for good. I’ve just decided to go with the flow and continue planning the wedding.

Feeling Bad

Dear FB,

I know you’re tormented by your situation. But let’s look at the facts on the ground: You worry that you and your fiancé “don’t go deep enough.” The sex is ok but not great. You pushed to get engaged, but shortly thereafter you had an affair. You’ve been very depressed in the past and had an eating disorder. He cheated on you. You cheated on him. You’re depressed again.

Even if we limit our considerations to the mediocre sex, the wondering if there’s something missing, and the suspicions about not going deep enough, this marriage gets a big thumb down from me. In my own experience, this combination of mediocrity/disappointment/shallow connections doesn’t pan out well. Longing for a deeper connection is not good. Throw in blah sex to match, and you’re talking about a major disconnect that’s going to haunt you every single day you’re together. You might be used to him, you might need him emotionally and you might be accustomed to seeing him as “the one.” But that doesn’t change the recurring suspicion that he’s not ultimately right for you.

You fought for the relationship for so many years that you’re simply accustomed to putting the relationship on a pedestal, in spite of many clear signs that you’re not an amazing match. You wanted to WIN him, to convince him that he was THE ONE. You wanted to wrap things up, “start [your] future,” “be on solid ground.” You were depressed and needy and unsure of what your life might look like, and you thought that if you could JUST secure your relationship status, you might feel safe and sound for once.

And sweet Lordy on high, I can relate to that. Fuck yes I can. Because for me, nothing was more frightening than graduating from college and getting booted out into the real world. I didn’t want to do ANYTHING back then. I wasn’t excited about the adventure of it all. I just wanted to hide. And even when my life was kind of adventurous, moving to San Francisco after living in North Carolina my whole life, getting a job downtown, mingling with the big city folk, I was just meh about the whole thing. I wrote sad poetry. I went home and cried to my noncommittal college boyfriend, who was all “Ew, go away.” So then I yelled, because I was a fucking crazy person. I threw the pumpkin out the window on Halloween. (I did not kill anyone on the street below, thankfully.) The next morning when I went to catch the bus to my shitty secretarial job, the sidewalk was covered in pumpkin slime. When I got to work, I wrote a sad poem about it. A BAD poem, that was also a SAD poem.

I tried to show my bad, sad poem to my boyfriend, of course, but he was all, “Ew, go away.”

But if I told my husband that story about the pumpkin — again! — he would smile and laugh. He likes hearing my dreary little tales. He understands how it feels to be pathetic, to do stupid shit, to act like a fucking crazy person, to feel sorry for yourself, to laugh about it years later. And to STILL feel a little sorry for your pathetic bad-poetry-writing self.

The two of us talk about this kind of bullshit all the time. And I’ve had maybe one other boyfriend — out of, I don’t know, fifteen? — who would enjoy a really pathetic story the way we do. The others would just want me to get to the point, or take my fucking pants off already. That kind of disconnect affects the quality of the sex you’re having, too. I’m not saying you always need to make the sweet slow sensitive emo boy love. NAY. I’m saying your perception of how deep the connection is MATTERS TO A HUGE FUCKING EXTENT.

As clearly as I recognize that you couldn’t give less of a shit about my stupid husband’s appreciation of my bad personality, I inject this here because when I was younger, I always treated major doubts about a relationship as something to push aside or hurdle over or stuff under the bed or, best of all, eliminate entirely. Major doubts made me unhappy, so I mostly wanted them to GO THE FUCK AWAY.

I was so wrong. Because major, repeating, inescapable doubts — about things like how good the sex is, how deep your connection is, whether or not there’s something missing — they are IMPORTANT. If you have giant doubts that won’t go away, to the extent that you’re clandestinely almost-fucking other people? You should not marry the dude.

SO: Even if you seemed totally healthy and happy and had dated 15,000 other guys, I would still say this really is not your guy. But–newsflash!–you do NOT seem totally healthy and happy and you have not dated other guys AT ALL. Instead, you seem like someone who has spent the past few years wanting to figure things out, nail things down, get ‘er done, etc. And look, having been there, I have to say, you just aren’t ready to make the call. You’re easily depressed, you don’t know what other guys are like, you’re a little needy, a little rash, a little confused. This is not a good time to make a lifelong commitment. You are very afraid. You may even be so afraid that you started that affair because you thought a brand new relationship would provide you with the perfect safe escape hatch from this one. Maybe you wanted to give yourself a safe place to land, because you’re afraid of being alone.

I don’t think you’re ready to get married to ANYONE, honestly. You have a lot of self-knowledge to gain. You need to figure out how to make yourself happy independently, without anyone in your life.

But even if that weren’t the case, your doubts don’t sound like a typical case of cold feet. You want a deeper connection, and better sex. You have many, many years left to find it. Breaking up will give you time to get to know yourself better, to make closer friendships, to become stronger, to clarify what’s important to you.

I remember a friend of my mom’s saying that I should make a list of the things I would NOT compromise on when it came to men. That made me laugh, because I’d basically never had any standards at all. It was just “Does he turn me on or not?” But do you know what turned me on back then? A whiff of escapism, or a faint hint of indifference.

You don’t want to be getting a divorce ten years from now, with two little kids under your roof, because you were never sure. You need to be alone for a while and sort yourself out and grow up. Your doubts are telling you something. You aren’t doing your fiancé any favors by keeping them to yourself. You spent so much time chasing him that you didn’t realize that you weren’t that into him after all, and you definitely weren’t ready to settle down. A few years from now, when you DO finally have a deep connection with someone, when you can tell that person anything and everything, and he listens and gets it, and you have great sex and you just KNOW that you are a great pair? You will be very, very glad that you didn’t go with flow way back when.

Put another way: If you were your own daughter, and she asked you, “Should I go through with it and marry this guy?” — what would you say? If my daughter asked me that, I would say “Be brave, and hold out for something that feels complete. Hold out until YOU feel complete.”


Do you feel complete? Write to Polly!

Heather Havrilesky (aka Polly Esther) is The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses. Photo by Gabriel Saldana.